Ben Cherington’s best trades show why he can't be trusted with Pirates' deadline

Ben Cherington has been the Pittsburgh Pirates’ general manager since November 2019. While he lost nearly a whole year to COVID in 2020, he has essentially been part of the organization for almost five full MLB seasons. While he has acquired some good pitching, that’s about where the positives end. The Pirates need hitting, and they could obtain that by trading some controllable players, like Mitch Keller, David Bednar, and Dennis Santana. He cannot be trusted to find hitting by dealing away players such as these.

The Pirates’ five most productive position players (per fWAR) they’ve acquired via trade since Cherington took over are dismal at best. The most fWAR any of them has racked up is Jack Suwinski, sitting at +2.2. Most of that was accrued during his first two years in the Major Leagues. Suwinski got off to a solid start to his MLB career, especially in his 2023 sophomore campaign. He swatted 26 home runs with a .793 OPS, .341 wOBA, and 112 wRC+. He had the ninth-most homers by an NL outfielder between 2022 and 2023 with 45. Thanks to his solid defense in center field, he put up +2.6 fWAR.

But since then, Suwinski has only appeared in parts of 112 games. After hitting nearly 50 home runs between two seasons, Suwinski has gone yard just ten times. His OPS has fallen well below .600 at .558, and his wOBA clocks in nearly 100 points lower than it did in 2023, sitting at .246. That has led to his wRC+ plummeting to just 52. Suwinski’s -1.6 fWAR is the third-least among any NL position player. So far, his fWAR with the Pirates is a meager +2.2.

Even Ben Cherington's best offensive addition with Pirates falls flat

Next up is Connor Joe. Most of Joe’s +1.9 fWAR was collected in 2023, when he turned in a solid .247/.339/.421 triple-slash and 106 wRC+. He was also a solid defensive corner outfielder/first baseman. He had +1.4 fWAR in only 472 trips to the plate. The next year, however, Joe slashed just .228/.320/.368 with a wRC+ of 92. His defense in the outfield and at first base was about the only thing that kept him from being a sub-replacement level player, adding just +0.5 to the Pirates' ledger. Joe was non-tendered by the Pirates after the 2024 season. He has since bounced around with the San Diego Padres and is now on the Cincinnati Reds.

The third-highest mark is Joey Bart at +1.6. The Pirates acquired Bart in early April 2024 and he took the city by storm. By the end of the season, Bart had a .265/.337/.462 slashline and 120 wRC+. Bart provided a ton of pop, going yard 13 times in only 282 plate appearances. His defense was lackluster, but his +1.3 fWAR was great for a catcher who only appeared in 82 games. Bart is still reaching base at a respectable rate this year with a .327 OBP and 11.1% walk rate, but his power is all but gone. He has only hit one home run in 226 plate appearances. Now, his fWAR is only +0.3.

Another 2024 acquisition was Isiah Kiner-Falefa. IKF was a trade deadline pickup, but struggled badly down the line with the Pirates last season. He had a sub-.600 OPS, with only a .257 wOBA and 60 wRC+ after the Bucs acquired him. His numbers have rebounded to a degree in 2025, with a .661 OPS, a .294 wOBA, and an 84 wRC+, but they are still subpar. His defense at shortstop is playable, but not excellent. His fWAR with the Pirates is below +1.0, sitting at just +0.6 in parts of 136 games.

The fifth-most fWAR any Ben Cherington position trade acquisition has picked up comes from ... Billy Cook. Cook was also a trade deadline acquisition, this time from the Baltimore Orioles, with nearly all of his Major League playing time coming in 2024. He appeared in 16 games with 49 plate appearances in a late-season sample size. While he hit three home runs with two doubles, Cook also struck out 19 times with no walks. He looked great in the outfield with +6 defensive runs saved and +2 outs above average in less than 100 innings. Cook also flashed a solid glove at first base. He has appeared in three contests in 2025, but the Pirates have kept him at Triple-A for much of the season. His fWAR with the Pirates is +0.3.

The only thing you can say in Cherington’s defense here is that the Pirates didn’t give up much of note for any of these players. The player the Pirates traded for Connor Joe is no longer in affiliated ball. They sent a relief prospect who has a 4.40 ERA and 11.9% walk rate to the SF Giants for Joey Bart. The prospect who was used to acquire IKF has a solid bottom line, but is striking out 31.2% of the time at Double-A. Cook cost the Pirates a pitching prospect who has been hurt most of the year. Only Suwinski was acquired using a real piece, that being Adam Frazier. However, he struggled badly down the line with the SD Padres, and was salary dumped just a few months later for players who are no longer in their organization, either.

However, in cases where the Pirates did trade a good/proven player for a deal where a position player was a noteworthy part of the return, Cherington has done poorly in this aspect, too. Jacob Stallings netted the Pirates former first-round pick Connor Scott, a player Pittsburgh released after two dismal years at Altoona. Joe Musgrove got the Pirates Hudson Head, who has a career 30.9% K% and .709 OPS in the minor leagues, and just made it to Double-A. Neither Maikol Escotto or Canaan Smith-Njigba, who the Pirates got from Jameson Taillon, panned out. Liover Peguero, who headlined the Starling Marte swap, has done very little in the Major Leagues (although the Diamondbacks didn’t get much out of Marte, either).

What reason is there for anyone to trust Cherington to trade some of their controllable Major League pitching for hitting, when the hitting he has put together has led to fewer runs scored per game than in the Deadball Era, and his attempts to acquire hitters via trade have led to very little? Suwinski, Joe, IKF, Bart, and Cook have a combined +5.0 fWAR. There are already three Major League batters this year alone with that high of a mark.

Jack Suwinski is the best Ben Cherington has done in five full MLB seasons when it comes to acquiring young position players. That means the Pirates cannot let him negotiate a trade involving Mitch Keller, Dennis Santana, David Bednar, or anyone else who isn’t a free agent at the end of 2025. A major part of the reason the Pirates have 18 losses where the pitching has allowed three or fewer earned runs this season is because Ben Cherington doesn’t seem to know how to build an offense, and letting him trade three of the Pirates’ most pivotal pitchers on their depth chart for the hope he can find some decent hitting is foolish at best, and complete incompetence at worse. This summer certainly has the chance to set the team back even further.